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Chapter 8: Q54b (page 262)

Question: Which of the following alcohols could notbe made selectively by hydroboration–oxidation of an alkene? Explain.

Short Answer

Expert verified

Answer

Possible

Step by step solution

01

Step 1: Anti-markovnikov’s rule

In hydroboration-oxidation reaction two steps occur:

  • Hydroboration- It occurs in an anti-Markovnikov manner, where hydrogen (from BH3) attaches to the more substituted carbon and BH2to less substituted carbon in double-bonded carbon. It is syn addition which means that the hydroboration takes place on the same face of the double bond.
  • Oxidation step involves the replacement of BH2 with hydroxyl group.
02

 Step 2: Alcohol possible or not:

Given alcohol is possible when a double bond is between C2and C3 as both are equally substituted so can attach to any side. Other alcohol possible is the same as given. Thus, this alcohol is made selectively.

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Most popular questions from this chapter

Dichlorocarbene can be generated by heating sodium trichloroacetate.

Propose a mechanism for the reaction, and use curved arrows to indicate

the movement of electrons in each step. What relationship does

your mechanism bear to the base-induced elimination of HCl from

chloroform?

Iodine azide, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as 1-butene isused, only one product results:

a) Add lone-pair electrons to the structure shown for, and draw a

second resonance form for the molecule.

10-Bromo-a-chamigrene, a compound isolated from marine algae, isthought to be biosynthesized from g-bisabolene by the following route:

Draw the structures of the intermediate bromonium and cyclic carbocation,and propose mechanisms for all three steps.

Iodine azide,, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as 1-butene is used, only one product results:

c)

In light of the result observed when,adds to 1-butene, what is

the polarity of thebond? Propose a mechanism for the reaction

using curved arrows to show the electron flow in each step.

Hydroxylation of cis-2-butene with OsO4yields a different product than hydroxylation of trans-2-butene. Draw the structure, show the stereochemistry of each product, and explain the difference between them.
See all solutions

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